


Cassidy to Castiel

by NEG85



Category: Supernatural
Genre: Angst and Hurt/Comfort, Assumed Relationship, Bobby Singer is Dean and Sam Winchester's Parent, Car Sex, Castiel Loves Dean Winchester, Castiel Talks Dirty (Supernatural), Castiel/Dean Winchester First Kiss, Castiel/Dean Winchester Mutual Pining, College | University Students Castiel/Dean Winchester, Consensual Sex, Consensual Underage Sex, Cute Castiel/Dean Winchester, Dean Winchester Loves Castiel, Dean Winchester Talks Dirty, Eventual Happy Ending, Explicit Language, Explicit Sexual Content, F/F, F/M, Family Drama, Fluff and Smut, Grief/Mourning, High School Castiel/Dean Winchester, Human Castiel (Supernatural), Hurt Castiel (Supernatural), Hurt Dean Winchester, Implied/Referenced Cheating, LGBTQ Ally Sam Winchester, LGBTQ Character, LGBTQ Themes, Loss of Parent(s), M/M, Making Out in the Impala (Supernatural), Minor Character Death, Misunderstandings, Name Changes, Not Cheating, Oral Sex, Parent Death, Praise Kink, Sex in/on the Impala (Supernatural), Teenage Drama, Teenagers, Trans Castiel (Supernatural), Trans Character, Vaginal Fingering, Vaginal Sex
Language: English
Status: In-Progress
Published: 2021-02-17
Updated: 2021-03-10
Packaged: 2021-03-12 03:46:50
Rating: Explicit
Warnings: Underage
Chapters: 11
Words: 18,255
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29503611
Author URL: https://archiveofourown.org/users/NEG85/pseuds/NEG85
Summary: Please don't hate me, but I feel like the story needs more angst and pining, so I might end up adding to the chapters and/or changing  them around without changing the what's already written- hope that makes sense. Or I may just add more chapters that go back and go into more detail about things that happened and were kind of glossed over and just mentioned.
Relationships: Castiel/Dean Winchester, Charlie Bradbury & Dean Winchester, Charlie Bradbury/Jo Harvelle, Ellen Harvelle/Bobby Singer, God | Chuck Shurley/Naomi, Lisa Braeden/Dean Winchester
Kudos: 23





	1. Chapter 1

**Author's Note:**

> Please don't hate me, but I feel like the story needs more angst and pining, so I might end up adding to the chapters and/or changing them around without changing the what's already written- hope that makes sense. Or I may just add more chapters that go back and go into more detail about things that happened and were kind of glossed over and just mentioned.

Cassidy Novak and Charlene Bradbury are best friends. Cassidy is 16 and Charlene is 17 (a four month difference, down to the day). Cas, as almost everyone calls her, has long wavy almost black hair, bright blue eyes and only recently dropped out of cheerleading after successfully convincing her parents that she was afraid it would start to ‘affect her grades’.

Charlene (Charlie to her close friends) has long straight auburn hair, dark green eyes and plays soccer, volleyball and softball. She also makes straight A’s and always dresses in comfy oversized clothes.

Cas and Charlie stand beside their shared locker talking, when a muscular arm slips around Cas’ shoulder.

"Hey beautiful." Dean says as he smirks at his girlfriend. His short blonde hair is spiked, like usual- a stark contrast to the almost military style cut. 

Dean Winchester is 17 years old, has broad shoulders, a muscular build and freckles that perfectly frame his emerald eyes. He’s been the star of the basketball and football team since jv, drives a hand-me-down ‘67 impala he calls ‘baby’, and he’s been dating Cas for a little over a year.

"Hey gorgeous." Cas replies, kissing his cheek and blushing.

"You guys are so cute together, it's disgusting." Charlie comments, shaking her head with a smile. "Don't be late for class again Cas, or Mr. Bennet will bite your head off." She adds as she walks away.

"So, whatcha doing after school today?" Dean asks with a mischievous grin.

“I don’t know. But, don’t you have practice?” she asks, wrapping her arms around his back.

Dean leans forward, slides his arms around her waist and walks her backwards until she’s against the wall beside the lockers. Dipping his mouth to Cas’ neck, he places a few teasing kisses. “Nope, it was cancelled.” he answers, before pulling the thin cotton fabric down to reveal the top of her right shoulder. He leaves soft lingering kisses across the newly exposed flesh, causing Cas to gasp.

Pushing him back a little, she looks up at him through her long dark lashes with mock innocence. “What’d you have in mind?” 

Almost growling, Dean leans forward again, this time whispering right beside her ear. He slides his hand down her arm and takes hold of her hand, rubbing it lightly against his growing erection. “Want me to fuck you after school today, Angel?”

“Gonna gimme a ride?” Cas asks, teasingly before she winks. Her eyes flick down to his bulging crotch then back to look him in the eye with a smirk.

“Fuck yeah. See you after class, babe.” He teases the tip of his tongue across her lips just as the bell rings. Winking at her just before he turns to walk away, she grins back, flipping him off before heading to Algebra.

“Ah, Ms. Novak. Thank you for gracing us with your presence.” Mr. Bennet says sarcastically as Cas enters the room.

She tries not to blush with embarrassment as a few of the jocks chuckle at the teacher’s words.

“Forget those assholes.” Charlie whispers, bumping her shoulder lightly against Cas’.

“I’d like to speak with you after class, Ms. Novak.”

A super mature “Oooh.” comes from the three boys and Cas rolls her eyes. “Yes, sir.” she answers simply, hoping to move along to the actual material.

Thankfully for Cas, the rest of class is unremarkable and she almost forgets about staying after until the bell rings.

“Want me to wait for you?” Charlie asks, hesitating at the door.

“Nah, go ahead. Dean’s giving me a ride home today anyway.”

“Ahh, gotcha. Alright, well see ya tomorrow.”

Once the class is empty besides herself and Mr. Bennet, she walks from the door up to in front of his desk. She looks down at him still sitting as he writes something in a small notebook. Not trying to pry, she looks away waiting impatiently for him to speak so she can get on with the rest of her day. She drums her fingers lightly on her Algebra book and apparently zones out. The next thing she knows, Mr. Bennet is saying her name with a deep sigh.

Shaking her head and focusing her eyes, she looks back at him. “Sir?”

“Ms. Novak, it seems that being tardy to my class is becoming a bit of a habit. “Would you disagree with that statement?” he asks, sitting on the corner of his desk crossing his arms.

“No, sir.” she answers simply, dreading the ‘concerned dad’ type of talk he was sure to give her.

“Good. It seems we’re communicating. Now, are there some medical factors I’m unaware of that seem to be interfering with you arriving on time to my class?”

“No, sir.”

“Well, your grades remain unaffected, for now, however I’m just concerned that this type of bad habit will leak over and encourage other, more harmful habits.”

Cas is completely lost now and decides to just nod occasionally as she watches Mr. Bennet’s mouth move. He may as well be speaking another language because she had no idea what he was saying. Finally after what feels like 30 minutes, he sighs and stops talking.

“Will that be all, sir?” she asks, walking toward the door.

“Yes, Ms. Novak. I hope you’ll think about what we talked about.”

Forcing a half smile, she nods and can’t get outside fast enough. As soon as she walks into the parking lot, she spots Dean’s car with him standing leaning against the driver’s side door.

“Hey, there you are. Is everything okay?” Dean says when he sees her a few feet away.

“Yeah, just Mr. Bennet again.” Cas groans and rolls her eyes.

Dean kisses her cheek. “Hop in, babe.” he says, opening his own door.

She quickly walks around, gets in and a moment later they are headed to her house.

The house is empty, like she knew it would be.

They both get out and Dean takes Cas' hand as they walk to the front door.

She unlocks it and they head upstairs to her bedroom.

As soon as her bedroom door is closed, she locks it behind them and saunters over to where Dean is sitting on the edge of her bed. She climbs into his lap, straddling him as she grins and puts her arms around his neck.

"Hi." She says as she leans in.

"Hey." Dean replies before their lips meet.

Dean's hands slide down around her waist and pull her impossibly closer as their tongues dance and explore each other's mouth for the millionth time.

She pulls back, moving to alternate between peppering Dean's neck with soft kisses and strong sucks.

"Oh god." He moans, gripping her hips tighter.

"You like that?" Cas teases before slipping her hands under his shirt. She caresses all along the flesh of his back and shoulders humming with pleasure.

"Yeah, love your mouth and hands on me, Cas." Dean answers crashing their mouths together again.

Cas melts into their deep sloppy kiss and begins rocking her body against Dean's.

Moaning, Dean lays back and pulls her down with him. He rolls them over until he’s lying on top of her.

Cas moans at him taking control and lets Dean grab both her wrists and hold them above her head.

Feeling wetness between her legs, she licks her lips and gasps when she feels her boyfriend lift her skirt. His still clothed cock presses against the thin cotton of her pink panties as he grinds against her.

Moaning at the sensation of her boyfriend's bulging thickness pressing against her, she sees Dean grin.

"You like feeling how hard you make me?"

Cas bites her lip and nods. "Please touch me, baby.

"Mmm yeah? What do you want, sweetheart?" Dean asks, rubbing against her again. "Where and how do you want me to touch you, Angel?"

She shifts a little and spreads her legs even farther apart. "Wanna feel your fingers baby. And your mouth."

Unlike most teenage boys, Dean liked tits just fine, they just weren’t something that particularly did much for him. Eating pussy, on the other hand, that was something he thoroughly enjoyed. For him it was the act of giving his partner pleasure, completely wrecking them with only his tongue. It was simply a bonus for him that the lucky recipient’s noises and faces of pleasure drove him closer to his own orgasm. Last but not least, selfishly, his favorite part was that when he did finally drive her over the edge he got to taste that pure scrumptious treat that nothing else could quite compare to.

Dean carefully pulls her panties to the side and moans as he sees the evidence of her arousal. He gently rubs his first and middle fingertips against her wetness, watching her face show her obvious pleasure. Slowly he sinks his two fingers deeper until they are inside the wet heat of her body. He feels his dick twitch as he begins to fuck into her with his fingers and she begins to pant and moan. She grabs his wrist pulling it towards her, urging him to move as hard and deep as he can. With every exhale, moans escape from her and her chest heaves as her body shakes. The pleasure causes pressure to mount to her building orgasm. Dean pulls his fingers out and licks them clean. Cas whines, and Dean grins, then leans in and licks straight on her clit before rubbing it gently with his thumb, earning him a gasp followed by more moaning. Grinning, he watches Cas squirm, still holding her wrists above her head. Sliding down until his knees are one the carpet, he continues stimulating her clit as he spreads her open. "Want me to lick your delicious pussy, Angel?" He asks, teasing his tongue against the wetness dripping down her thighs.

Cas moans. "Mmm yes, please. Eat my pussy, baby." She begs.

At that, Dean begins to draw out moans and more wetness from his girlfriend that only drives them both on. He tongues right around her opening then immediately buries it inside her hot delicate inner flesh. He can hardly wait til he has her cumming on his tongue so he can lap it up drinking it down.

Cas' moans get longer and louder as he continues sliding his tongue along every inch of the inside of her pussy and diving it as deep as he possibly can inside her. 

Dean alternates between hums of contentment and moans of arousal as he drives Cas wild. 

She begins writhing below him. The heat pools low in her belly as she feels the need to cum building. 

His so far neglected dick is hard as a rock as he keeps pushing her towards her orgasm.

"Oh god, Dean. Mmmm fuck baby. Oh yeah baby fuck your tongue is amazing." She cries out through panting, gasping and moaning.

Dean stops for a second and pulls back. "Your pussy tastes so fucking good. Cum for me, cum on my tongue, Angel." He answers before getting back to his mission.

A few moments later her body stiffens beneath him, moaning with eyes closed tightly as her orgasm washes over her.

Dean moans loudly as he's rewarded with that amazing delicious flavor on his tongue. He swallows it all down eagerly then eases his grip on Cas' hips.

She twitches, still panting as he releases her wrists and kisses her needy, eager and sloppy. Tasting the remnant of herself on Dean's tongue, she knows that now he is insanely hard and needing release of his own.

"Mmmm thank you baby. Now it's my turn to make you feel good." Cas says rolling them back over. "Just lay back and relax and let me take care of you." Unzipping and unbuttoning, she opens the fly of his jeans and he helpfully lifts his hips so she’s able to pull the jeans and boxers down to his ankles.

Dean's painfully hard erection is finally free, the head dripping with precum. Cas dips her head down and licks across his slit collecting his small clear mess as she wraps her fingers around his thick cock and begins to jerk.

Sucking in a breath, his toes curl at the sudden heat and wetness of Cas' mouth on his sensitive flesh.

Moving down, her mouth seals around Dean's thick shaft taking his length into her mouth.

"Oh yeah, feels so good, Cas." Dean moans desperately grasping the covers with one hand as the other gently pets against the back of Cas' head.

She continues taking him down as far as she can as she continues to stroke him for a few minutes until she suddenly pulls back. Dean whines.

"I wanna ride your cock baby." Cas says, crawling up to straddle him again. Pulling her panties to the side she holds Dean's shaft against her opening before sliding down onto it.

"Oh fuck. God you're pussy is so tight, sweetheart." Dean moans, not moving. "Such a good little slut for my cock, baby.”

"Fuck yeah, love being your slut, baby." She grins as she slips down all the way til every bit of Dean's cock is inside her.

"Gimme a sec." Dean warns, holding Cas' hips still.

Several seconds pass and Dean gently grips Cas' face and pulls her down to him. "Kiss me."

She does, and waits a couple more seconds before she firmly places her hands against Dean's hips and begins to move. Slowly at first, she gradually increases the speed of her thrusts as she moans and listens to Dean’s noises feeling his fingers dig into her skin.

Dean watches her ride his cock and can't help but be turned on at the fact that Cas is still fully clothed, panties pulled to the side as she uses him to fuck herself. "Fuck yeah, ride me Angel." He moans and begins to buck his hips up to meet her thrusts.

Cas throws her head back, eyes closed and face twisting in pleasure as their rough thrusts send her quickly towards another orgasm.

“Yeah, cum for me, Angel. Don’t stop, baby.”

He feels her pussy spasming as she’s pushed over the edge again. She’s almost shouting at the release.

Panting, she thrusts down more vigorously. As deep and fast as she can to bring her boyfriend to his climax.

“You gonna cum for me, baby? You love fucking my slutty pussy, don't you? This pussy's only for you, Dean.” she knows dirty talk will get him there faster.

“Fuck yeah baby. I’m gonna cum for you. Yeah, this cock's only for you, sweetheart. Want me to fill your pussy up, Angel?” he asks through gritted teeth.

She can tell he’s about to finish now. "Yes please, fill me up, just like I like, baby. Yeah, I love being your cumslut.”

“Oh god. Fuck yeah.” he answers right before stilling and holding his breath.

Cas gasps as she feels his warm cum fill her pussy. “Mmmm. love it when you cum in me.” she says, kissing him before leaning up slowly.

His softening dick slips out as she climbs over to lay beside him.

He looks over at her and smiles.

“What?” she asks, blushing.

“You’re so perfect for me, Angel.”

Cas blushes furiously, burying her face in her pillow.

“I mean it.” he says, gently pulling her back face him.

“I think you're perfect for me, too.” she says, rolling to face him and nuzzling her face against his neck.

He wraps his arms around her and breathes in her scent. “I love you, Cas.”

She pulls back a little and looks at him for a moment. “You’ve never said that before.” she finally replies.

“Yeah, I know. But...I do. I love you.”

She chuckles, feeling tears sting her eyes. She cups his face and kisses him gently. “I love you too, Dean.”


	2. Chapter 2

A few months later, her parents let her throw a small party for her birthday. They promised to stay clear of the party as long as Cas promised there wouldn’t be any drinking or other types of ‘hooligan’ behavior. She assured them that they could trust her.

Taking the opportunity to have a date night, her parents Chuck and Naomi said they were going to dinner then to the movies. They assumed that would be a reasonable amount of time to enjoy the festivities of her celebration.

After they left, Dean was the first one to show up at her door. “Hey baby.” he says, pulling out a bouquet of red roses from behind his back.

Her hands automatically cover her mouth in surprise. “Oh my god, babe! They’re beautiful!” she says grinning and pulls him inside. “Thank you, Dean.”

“Beautiful flowers for a beautiful girl.” he says, smoothe as usual.

Her smile fades a little as she turns away. “Gonna put these in some water. Be right back.”

Dean wonders if he did something wrong.

After a few minutes she comes back in and sits down in the living room. He joins her on the couch and takes her hand. “I’ve missed you. Seems like we haven’t seen each other much lately. Is everything...are we okay?” he asks with a concerned look.

She fakes a smile, but he can tell it’s not genuine.

“Babe, whatever it is, you can tell me.” he says, attempting to reassure her.

The doorbell rings and she hops up to answer it. Charlie enters, with Benny and Anna behind her.

“Hey guys. Thanks for coming.” Cas says, hugging Charlie then Anna.

“Of course.” Charlie says, walking over to Dean. “Hey man, how’s it going? Haven’t seen you around lately.”

Dean’s not sure what to say to that. ‘Does she know what’s going on with Cas?’ he thinks to himself. ‘Surely she would know, she’s her best friend.’

“Hey Charlie.” he finally responds, ignoring the question.

This is my cousin Benny and of course you know Anna from school.” Charlie says.

“Nice to meet you Benny.” Dean feigns a smile, nodding to the other boy.

“You too, Dean. I’ve heard all about you.” Benny answers.

‘What the hell does that mean?!’ Dean wonders curiously. “Uh, I think I’m gonna go see what there is to drink.” he says motioning toward the kitchen.

“Did I say something wrong?” Benny asks Charlie.

“Nah, Dean’s just uh...I think he’s been going through a rough time lately, that’s all.”

“Oh, okay.”

Charlie hates lying, but honestly she has no idea what’s going on between Dean and Cas lately. Cas is obviously hiding something and refuses to open up, even to her. She feels bad for Dean because it's more than obvious he loves Cas, but she’s been constantly blowing him off.

Several more people arrive and Cas and Dean bring out the snacks and drinks to the large folding table.

Dean watches as Cas makes rounds to everyone talking and laughing. He loves seeing her happy and is glad she seems to be having a good time. After she has talked to everyone, she stands beside Charlie in the corner of the room.

He gulps, feeling his heart start to race as he makes his way over. “Cas, can we talk for a minute?” he asks hesitantly.

Charlie quickly darts her eyes away from him and back to Cas, giving some kind of look he doesn’t recognize. “Uh, sure. Let’s uh...let’s go to the kitchen.” she says, walking away. He follows behind and his heart sinks as she turns to face him.

“Cas...do you even want me here?” he asks.

She gives him a strange look, then darts her eyes to the floor. “I invited you, didn’t I?”

“That doesn’t answer my question.” he insists.

She takes a deep breath, still not looking at him.

“Did I do something wrong? Did I piss you off or hurt your feelings or something?”

“No, of course not.”

“Then what’s going on?”

She sighs, still looking at the floor.

He takes her hand gently. “Cas, please talk to me. Can’t you even stand to look at me?”

She looks up at him with unshed tears filling her eyes. “Dean, I….I don’t know what to say.”

“Tell me you still love me?” he asks, feeling tears sting his eyes.

“I...Dean I’m dealing with a lot right now. I’ve.. there’s some things I’m trying to work through, okay? Can you...I just need some space.” She answers, struggling to find the right words. She can see on his face that she’s hurting him, but she doesn’t know the right thing to do.

“You know you can talk to me, tell me anything, baby. I’m here. Whatever it is, maybe I can help. Please..can I just be there for you?”

"I think I need some time. And some space- away from you.”

His face changes immediately from vulnerable to guarded and he scoffs. “Right, away from ME. You GOT it.” he spits the words out as he walks right out the front door.

Charlie immediately comes into the kitchen. “What the hell, Cas? What’s going on? Why did Dean just leave in the middle of your party?”

“Charlie, I don’t wanna talk about this right now, okay? I just...I can’t...I just wanna try to enjoy the rest of the party.”

Charlie scoffs and shakes her head. “You know what, I'm REAL tired of this.” Charlie says, grabbing her coat. “I'll see you later. and Happy Birthday.” she says sarcastically as she walks out.

Dean is walking to his car and Charlie runs up to him. “Dean, wait.”

“Hey Charlie, uh..now’s not really a good time. I gotta go.”

“Wait, can we talk?” she says, looking at him with a little guilt.

He gulps and considers her offer. “What do you want.” he bites out.

"I wanted to talk about Cas." she offers, weakly.

He looks at her for a moment. "Fine, hope in."

She climbs in the passenger side and they start driving. She can tell he’s tense and seems really upset about whatever just happened.

He pulls over into the parking lot of an abandoned building and turns off the engine. Turning toward her he purses his lips together. “So, what is it? Do you know what the hell's going on with Cas lately?”

“I wish I did..but no. I just feel really shitty about Cas blowing you off all the time lately. But...I wanted to let you know you’re not the only one she’s pushing away. There’s obviously something going on with her, but she won’t talk to me about it. So, I been kinda pretending not to notice you haven’t been around her much.”

“Glad to know it’s not just me, I guess.” he scoffs. “I tried to talk to her, and she told me she needs space- from me.”

“Damn.”

Dean shoots her a look.

“Sorry. I just mean, that sucks. I wish I knew what to tell you, man.”

“Me too. So, you bailing on the party too, or you want a ride back to Cas' house?”

“I don’t think there’s any point in going back.” she says honestly.

“Looks like maybe you and I both lost someone close to us tonight.”

“Yep, kinda feels that way.” she agrees.

“Well, you feel like getting trashed?” Dean offers.

“You’re not hitting on me, are you?” she asks, looking at him skeptically.

“Hell no!”

She looks at him, eyes wide.

“Shit, I mean...I didn’t mean that like it sounded. Nothing against you, I just...Cas holds my heart.”

Charlie puts her hand on his shoulder. “I know she does, Dean. And the last I knew, you are holding hers too. And, look. Maybe we’re overreacting here. Maybe she does just need some time and space. Maybe from both of us.”

“I hope you’re right about that. It just...hurts that she needs to be away from me.”

“Yeah, I feel the same way. She’s been my best friend since the fourth grade and for the first time, she won’t talk to me about something that’s obviously bothering her a lot.”

“How about that drink?” he asks.

“Hell, why not. Apparently I have nothing else to do for the next few hours.”

“Alright, well let’s go then.” he says, starting the engine.


	3. Chapter 3

Upstairs in his bedroom, Sam is on the phone with his girlfriend when he hears laughing coming from downstairs. “Uh, Jess lemme call you back.” He cautiously goes to check it out, knowing that Dean wouldn’t be home until much later and their dad probably wouldn’t be back til tomorrow. He sees his brother and is a little confused by the image of him with another girl alone. “Uh, Dean what’s going on? Why aren’t you at Cas’ party?” Sam asks, skeptically eyeing the girl who he thought was supposed to be Cas’ friend. “Charlie?”

Dean and Charlie both look up at Sam from their positions on the floor. They are both sitting on opposite sides of the coffee table, empty beer cans strewn across it and a half empty Whiskey bottle directly in between them on the table.

“SAMMY!” Dean calls with a wide grin. “I love you, man!” he jumps up and throws his arms around Sam in a quite unexpected hug. “You’re the best little brother ever!” he proclaims. “Uh, yeah. Sure Dean, thanks.” he says barely managing to take a step back from Dean.

“Heya Sssam.” Charlie slurs, then giggles to herself.

Laughing loudly, Dean points to Charlie. “You’re DRUNK!” he accuses with a chuckle before nearly staggering into the wall.

“Look who’s talking, OTIS!” she cackles throwing her head back and tips over backwards landing on the soft carpet. “OOPS.” she adds, followed by uncontrollable laughter.

“Ugh.” Sam says, shaking his head. “Okay, what’s going on?” he asks, knowing full well he probably won’t get a real answer.

The other two’s attention quickly goes back to the younger boy and their smiles fade.

“Well?!” Sam insists.

“Me and Cas...shhhe doesn’t wanna see me, Sammy.” Dean says, looking sad now. “We had a fight but...I don’t know what I did wrong. What did I do wrong, Sammy?” He asks, tears rolling down his cheeks.

“She won’t talk to me either.” Charlie sobs. She sniffles and looks back to Sam. My BEST FRIEND won’t even tell me what’s going on with her.”

Sam closes his eyes, tips his head down and pinches the bridge of his nose with a sigh. “Have you guys tried to confront her about it?”

Dean and Charlie hug each other, still crying dramatically. “We tried Sam!” Charlie answers first. “She said she wants space- FROM ME Sammy. What if she doesn’t love me anymore?” Dean whimpers.

“Just what in the HELL is going on here?!” Bobby shouts, standing just inside the front door.

Charlie and Dean startle and turn to face the older man, stumbling over each other.

Sam sighs. “Dad-”

“Are you a part of whatever’s going on here?” he asks Sam, pointing to Dean and Charlie.

“No, I just found the two of ‘em like this a few minutes ago, I swear.”

“I believe you, son. Go on, I’ll take care of tweedle dee and tweedle dum.” he answers giving the other two a stern look. 

Sam shrugs and heads back up to his room.

Bobby sighs. “Alright, CHILDREN. Somebody needs to explain what the hell’s going on here. Spill it, you two.”

Dean and Charlie both glance at each other before their eyes go back to Bobby. They both start talking at the same time, sobbing, slurring and stuttering.

“Jesus.” Bobby says under his breath, rolling his eyes. Quickly realizing he’s not going to get anything intelligible out of them, he just shakes his head at them before heading upstairs.

*knock*knock*

“Come in.” Sam answers.

Bobby sighs. “Sam, did you manage to get anything coherent out of ‘em?”

“They both say Cas won’t talk to them. That something’s going on with her and she won’t say tell them what it is. Dean says she told him she needs space specifically from him.”

“Hmm. What about those two. Should I be concerned? Is there something going on between them I should know about?”

“Nah, I seriously doubt it. You’ve seen how much Dean’s eyes light up when Cas is around. I think whatever’s going on, they both just needed someone to talk to about her shutting them out.”

Bobby nods.

“Goodnight Dad.” Sam says yawning.

“Goodnight, son.” he answers.

Bobby tries to mentally prepare himself as he heads back down the stairs. Entering the living room, he spots Dean’s head down on the coffee table turned to the side with the whiskey bottle just out of his still outstretched hand. Charlie is lying on her back on the carpet. Both are snoring like logs. Bobby scrubs his hand over his face.

Doing his best to half drag, half carry Dean to the couch he manages to do a decent job, only his legs hanging off the side. Adjusting him the best he can, he moves on to Charlie. He carefully picks her up, bridal style and lays her on the loveseat. He lays a small blanket across each of them, then heads upstairs to bed.

\----------------------------------------------------------------------------------

The next morning Sam comes downstairs and walks through the empty living room. He hears someone moving around in the kitchen. “Morning.” He says, greeting his dad when he sees him standing at the stove.

“Hey, want some breakfast?” Bobby asks, glancing up from the frying pan.

“Sure. Hey, where’d Dean and Charlie go?” Sam asks as he takes a seat at the table.

“Last I checked, one was leaned over the toilet and the other leaned over the tub puking their guts out.”

“Sounds like fun, so sorry I missed out.” Sam chuckles.

“I made sure to let them know as soon as they’re done, they’re cleaning up their own mess.”

“Serves ‘em right.” Sam agrees.

“Alright, it’s ready, come fix your plate. I’m gonna go check on ‘em.”

Bobby peeks around the corner of the bathroom trying his best not to breathe in. “How’s it goin’ in here, guys?” They are both sitting up but still in front of their designated sick areas. “Ready to eat?” 

Charlie and Dean both groan in unison, causing Bobby to chuckle. “How about a drink?” he adds.

“Please stop.” Dean begs hanging his head back over the tub. “We’re sorry, Bobby.” Charlie adds.

Bobby laughs loudly. “Oh, I can tell. Soon as you’re done, come on downstairs so we can have a little chat.” he says as he walks away.

“Oh god, my head.” Charlie whines once Bobby leaves the room.

“Ugh! I didn’t think I’d ever stop throwing up.” Dean adds, wiping his mouth with a wet washcloth.

\-------------------------------------------------------------------------------------------

About 20 minutes later, they slowly make their way to the kitchen and sit at the table.

“So, now that you’re not crying your eyes out or unconscious how about you two tell me just what you were thinking with all that alcohol.”

“I’m sorry, Dad. Really. I know you must be disappointed in me, but...Cas...I don’t know what’s going on. She’s been blowing me off for the last month, I gave her some time and then tried to talk to her about it. She told me last night at her party that she needs some space away from me. And... it hurt like hell.”

“And what about you, Charlie?” Bobby asks, taking a bite of his eggs.

“Cas has been my best friend since the fourth grade and we’ve never kept secrets from each other before. She’s been acting a little strange lately and she won’t talk to me about it either. I guess I feel pretty hurt too. We’ve always been so close.”

“Well, I wish I had some advice to give you but sometimes people really do just need to work things out for themself. Maybe you two should just try to keep being patient with her. I’m sure she’ll come around.”

“Yeah, I hope you’re right.” Charlie answers.

“Thanks, Dad.” Dean says, finally chancing to glance up at Bobby’s face.

“And I’m not disappointed, Dean. Hell I remember what it’s like to be a teenager, even if it was back before they discovered the wheel.”

Dean and Charlie both chuckle at that.

“I will say I’m proud of you for not drinking and driving or drinking while you’re out and getting into trouble. But you’re way too young for me to look the other way while you get into my whiskey and drink a whole 12 pack between the two of you. Charlie, you’re not my kid, but while you’re in my home I expect the same out of you as I do these boys. Respect me, and I’ll respect you. Now, I’m not gonna tell your folks about your condition last night, and it’s none of my business whether you decide to or not. But let me just say, I don’t expect there to be a repeat occurrence here. Out of either of you. Do I make myself clear?”

“Yes sir.” They answer in unison.

“Good. Now if you think you’re over being sick, you need to go clean up the mess in the bathroom. Charlie, I’ll drive you home after you two are done with that.”

“Thank you. I appreciate that.” She answers.

“Dean, besides school and sports, you’re grounded. That means no driving if it’s not something falling in those categories that you’ve told me about beforehand. I’m gonna trust you to not to lie to me, unless you give me a reason to doubt you. That sound fair?”

“Yes, sir.”

Charlie and Dean both get up and scoot their chairs in, heading back upstairs.


	4. Chapter 4

After she gets home, Charlie’s parents ask how Cas’ party went. She decides to let them think she spent the night with her, like she had originally planned. She simply answered that it was tons of fun, and they left it at that.

Later on, she sits on her bed petting their orange long haired cat, Buster and calls Cas.

“Hey Mr. Novak, it's Charlie. May I speak with Cas?”

“You may indeed. “Cassidy, Charlene is on the phone for you, dear.” he calls out. “Here she comes now. Please give your parents regards from the missus and I.” he tells Charlie.

“Will, do, sir.” she answers politely, rolling her eyes.

“I got it, Dad.” Cas calls out from her room. There’s a *click* indicating he has hung up the living room phone. “So, did you have fun after leaving my party last night?” Cas asks snarkily.

Charlie assumes her tone is because she’s upset at her ditching and admittedly she does feel a little guilty. “Look, I’m sorry I left. I overreacted. I just-”

Cas cuts her off. “Wanna hear some juicy gossip I heard from Anna’s cousin Dana?”

“Uh..I guess, but-” Charlie starts to answer, confused at the change in topic.

“Dana told Anna, who told ME, that she saw YOU leaving Dean’s house this morning! And BENNY swears he saw you hop in Dean’s car last night right after you stormed out!” Cas states, accusingly.

“Cas, I-”

“SAVE IT. I MISTAKENLY thought we were supposed to be best friends, but I see now there’s clearly a lot I don’t know about you and who knows how long something’s been going on between you and Dean.”

“NO! Cas, I SWEAR, okay? Seriously, SWEAR ON MY LIFE I would NEVER do that to you!! Not EVER! Please, just let me explain.”

“Why don’t you stop wasting my time and just go hang out with your new boyfriend! You two deserve each other!” Cas snarls, slamming the phone down.

Charlie hears the dial tone and sighs as silent tears drip down her cheeks. She buries her face in her hands. She can’t believe this is happening.

Dean decides he’s not going to call Cas. He’s going to try to be patient and respect her wishes for space and time away from him, even though it sucks.

The whole next week he keeps his distance from Cas but can’t stop his eyes from lingering on her when he sees her in between classes. He suffers silently. At the end of the day on friday, he sees her walk out of the school building, about to walk home. He can’t resist the urge to offer to drive her. He’s desperate to be near her, even if it’s just for the short trip between school and her house. “Hey Cas.” he says, jogging to catch up with her. He stops beside her, noticing she’s stopped and is now looking at him like she’s pissed.

“What do YOU want?” Cas asks hatefully.

He’s thrown by her tone and the way her eyes seem to be filled with rage. “I, uh..sorry. I was just gonna see if maybe you want a ride home.” he tells her hesitantly.

Cas scoffs. “No thanks. Why don’t you ask your NEW girlfriend. I’m sure she’d appreciate ANOTHER ride in your super cool car.” she answers, sarcastically before walking away in a huff.

“Wait, WHAT?” he asks, catching up with her again, turning her shoulder to face him again.

She lets him turn her and she stands facing him again. Now with tears filling her eyes, the scowl on her face remains.

“Cas, baby, what are you talking about? New girlfriend?” I’m with YOU.” he insists, feeling his heart pound and sink into his stomach. Confusion and desperation are clear on his face.

“I KNOW about you and Charlie, Dean. Don’t bother denying it. I KNOW she stayed the night with you last weekend.” she shakes her head as she begins sobbing.

He cocks his head to the side, feeling like he can’t catch his breath at the obvious misunderstanding. “No, Cas I can explain. I promise, baby I only want YOU. NOTHING happened like that.” he tells her. His eyes pleading for her to believe him. “I’ve never lied to you, Cas.” he adds, trying to take her hand.

Cas jerks her hand back and silently turns and walks away.

‘FUCK!’ he thinks, his heart splintering. His eyes close, fighting back tears. Once he gets home, he calls around til he gets Charlie’s number.

“Hello?” Charlie answers, sounding as broken as he feels.

“Hey Charlie.” he says, with as much energy as he can extend.

“Dean?” she asks with surprise in her voice.

“Yeah, sorry. Hope you don’t mind, I called around til I got your number. Can we talk?”

“I don’t know if that’s such a good idea.” she sniffles. “Apparently Cas thinks something happened between us when I ended up staying the night last weekend.”

Dean sighs at hearing the terrible implication again. “Yeah, I know. I saw her today after school and...she hates me. She thinks we’re together now.”

“I mean, I guess I can admit it looks bad. But she should know us better than that.” Charlie insists.

“Yeah, I thought so too.” Dean agrees.

“You think there’s anything we can do to change her mind? Convince her that it’s not true?” Charlie asks, hoping for a reason to believe it.

“I honestly don’t know.”


	5. Chapter 5

The next few weeks Cas ignores Dean’s existence. He’s completely heartbroken. Word spreads about what supposedly happened between him and Charlie, so he loses some friends. Mostly the guys on his team are the only ones who don’t seem to mind whether the rumors are true or not.

Charlie sits alone at lunch and walks home alone after school. Not that she doesn’t have other friends, but none as close as she and Cas had been. And some who believe the rumors without even getting her side of the story stop talking to her.

2 months later….

The whole school seems to be going crazy over whatever the latest gossip is when Charlie gets to school.

“Oh my gosh, Charlie. Have you heard?” Amelia asks Charlie meeting her at her locker.

Charlie sighs. “I’m not really in the mood for high school drama, Amelia.”

“It’s Cas.” Amelia says matter-of-factly.

Her eyes dart to the other girl’s face. “What about her?” Charlie asks. A bad feeling comes over her as she waits for her answer.

“She’s gone.”

“What do you mean, gone?”

“Nobody knows where she is.”

“Wait, what are you talking about?”

“Her parents came and unenrolled her from school yesterday afternoon.”

“WHAT? Why would they do that?”

Amelia only shrugs. “Nobody seems to know what’s going on.”

Charlie’s mind is reeling and she struggles to process this information. “Are they moving or something?”

“Maybe.” Amelia offers weakly.

Panicking, she searches the crowded hallway until she finds Dean’s first period classroom. She peeks around the corner and sees him sitting at his desk. The bell is about to ring in a few minutes but she needs to talk to him. She walks in, grabs Dean’s arm and pulls him out into the hallway.

“Charlie, what-” he starts to ask.

“Have you heard about Cas?” she asks impatiently. Worry evident on her face.

“Wait, What about Cas, Charlie?” he asks.

“Apparently her parents came in yesterday afternoon and unenrolled her from school.”

“WHAT?!” Dean says a little too loud, causing several people to turn and look at him.

“Nobody knows what’s going on. But...everyone’s saying she’s gone.”

“Gone where?”

“Your guess is as good as mine.”

“Fuck.”

“I agree.”

Dean goes back to his desk and grabs his backpack. He walks back into the hallway and heads away from Charlie.

“Dean?” She jogs to catch up with him. “Wait.” she says.

He stops and looks at her.

“Where are you going?”

“I’m going to see what the hell’s going on.”

“How do you plan to do that?”

“I’m going to Cas’ house.”

Charlie seems to consider his words for several seconds. “I’m coming with you.” she tells him.

“Alright, let’s go.” he says.

They both rush out the door and hurry to his car.

Pulling up to Cas’ house, Mr. Novak’s car is gone, but Mrs. Novak’s car is in the driveway. They both run up to the front door. Looking at each other, Dean takes a deep breath and rings the doorbell.

The door opens and Mrs. Novak seems more than a little surprised to see them. “Hello, Charlene. Dean. What can I do for you?”

“Uh, Mrs. Novak may we please talk with Cas?” Charlie asks, with a fake smile.

“Please, ma’am we really need to speak with her.” Dean adds, his voice clearly displaying his desperation.

An uncomfortable look comes across the woman’s face and her eyes dart to the floor then back to them. “Cassidy no longer resides at this residence.” is her short reply before shutting the door in their faces.

Dean and Charlie look at each other quizzically. “What the fuck?” Dean asks.

“Exactly!” Charlie agrees.

This time Charlie rings the doorbell.

The door opens again and Mrs. Novak’s face is clearly showing her aggravation. “Yes?” she asks, obviously trying to be polite.

“What the hell’s going on?!” Dean demands, his gruff tone matching the no nonsense look on his face.

The woman’s eyes widen and she holds her hand to her chest. “My, what language Dean. I’m SURPRISED at you! How dare you speak that way to me!”

“How dare ME?! Where the hell is Cas? What the hell’s going on? What have you done with her?!” Dean growls, stepping up to the woman’s face.

Charlie’s eyes are wide as she’s shocked at Dean’s words and behavior. But honestly, she doesn’t disagree with him because she wants to know what’s going on too. “Please, Mrs. Novak. Dean and I both deserve to know where she is. That she’s okay. You’ve known me practically my whole life. I’m begging you.”

Mrs. Novak glares at Dean and he takes a step backwards. She looks at Charlie and she suddenly looks sad. “Please leave and don’t come back. We do not care to associate ourselves with her any longer.” This time she closes the door and locks the deadbolt.

The two teenagers are shocked into silence by Cas’ mom’s words. They slowly walk back to the impala.

Charlie gets lost in thought and when she comes back to herself, she sees them passing the school. “Where are we going?” she asks.

“You really in the mood to finish the school day?” he asks without taking his eyes off the road.

“Not really.” she admits.

They are silent until Dean pulls into the driveway of a run down abandoned house.

Charlie sighs.

“What did she mean? How could…” Dean trails off shaking his head.

“Shit, I have no idea.” Charlie admits. “This is unreal. Crazy even.”

Dean looks out his window, silently running through Mrs. Novak’s words and the possibilities of what could have caused her parents to disown her and send her away.

The months pass and Dean and Charlie become real friends. At first, they just vent to each other about the insane situation about Cas. But eventually they start to open up to each other about other things. Charlie shows Dean her comic book collection and how good she is at video games. She begins to see how smart he is, despite him claiming otherwise. She sees how good he is to his little brother and how he’s actually very kind. Rumors spread around school like crazy about them, but they don’t let it bother them. Before they know it, they’re best friends.

The day comes when the police show up at the school and of course everyone is chattering about it.

The bell rings and Dean see’s Charlie sitting in the office talking to the officers, curled up and bawling her eyes out. He instinctively hurries over to her and before any of the adults can stop him, he’s standing beside her. She jumps to her feet when she sees him, hugging him tight.

When Dean finally got the story, he found out that her parents had been in a car wreck. A semi lost control and crossed the median on the highway crashing into them. They were pronounced as soon as the ambulance arrived.

Dean is excused from school to give Charlie a ride to meet with her aunt.


	6. Chapter 6

Charlie’s aunt makes it abundantly clear that she has no intentions of taking on the responsibility of her only niece, despite being named legal guardian in her parents’ Will. While Charlie is relieved to not have to move with only four months until graduation, the state tries to convince her aunt to give custody over to put her in a foster home.

Dean tells their dad about the situation. Reluctantly, Bobby offers to let Charlie move in with them until she leaves for college. Before he agrees, he makes sure Sam is okay with it and then makes Dean and Charlie both promise to not get into any trouble until after they finish school.

Charlie comes home with Dean and Sam with her things packed and they move her into her new room in the attic. She hugs Bobby and he awkwardly hugs her back. “Just so you know, the only reason I had reservations about you moving in here is just the fact that I don’t know much about teenage girls. Hell, at this point you’re already family anyway.” he grins patting her back.

“Thanks Bobby.”

“Well, might as well get your room set up.”

She nods and heads upstairs.

“Dad, thank you for doing this for Charlie. It was hard losing mom, but I can’t imagine how hard it would be to lose both of you.” Dean says.

His dad is surprised as Dean leans in and hugs him, as Dean isn’t always the hugging type.

“Love you dad.” Dean adds when he pulls back.

“I love you too, son. Why don’t you go see if Charlie needs any help unpacking.”

“Alright.”

“I’m glad you’re here, Charlie.” Sam says, standing outside her door.

“Thanks, Sam. Me too.”

He walks in slowly, tears in his eyes and he hugs her. “I’m so sorry.” he adds, remembering how hard it was losing their mom.

She sniffles and her tears start to pour.

“I know I’m just a kid to you, but if you ever wanna talk sometime I’ll be here.”

“I appreciate that.” she tells him, wiping her eyes and trying to gain her composure. She sighs and pulls back. She forces a smile.

“I’ll give you your privacy.” Sam says, leaving the room.

Dean knocks on the open door.

Her head is turned away as she answers. “Come in.” her voice trembling.

“Sorry, is this a bad time?” Dean asks.

She shakes her head.

He walks in and sits on the edge of her bed, beside her.

“Wanna talk about it?”

She doesn’t speak, just turns and hugs him and cries harder.

He wants to say something, but knows from experience that nothing he can say or do will make her feel better or help with her pain. He simply holds her and lets her weep on his shoulder.

\-----------------------------------------------------------------------------------

A few days later, Bobby catches Dean as he’s heading to bed. “Hey, uh so how’s she doing?” he asks.

“As good as can be expected I guess. Hard to answer that, ya know?”

“Yeah I know. You’re a good friend, Dean. I’m glad Charlie has you to look out for her and to be there for her. I’m proud of you.”

“Thanks. She deserves it. She’s a great person.”

Bobby nods in agreement. “Goodnight, son.”

“Night Dad.”

\-----------------------------------------------------------------------------

Charlie and Dean both apply for the same out of state college and are accepted. By the time graduation rolls around, Bobby’s already gotten used to having a girl in the house again. He cries softly, standing and clapping along with Sam, for both teenagers when their names are called to walk across the stage.

They pack up their things and go to head out when Bobby and Sam meet them at the door. Hugs go around before the car is packed up. Watching them drive away, Bobby already feels their absence. Putting his arm around Sam, they head back inside. Sam cries because of course he’ll miss his brother but he’s also gotten much closer to Charlie since she moved in.

“I know, I’m gonna miss ‘em too. They’ll always be holidays and visits from both of ‘em during school breaks and stuff.” his dad says attempting to comfort both Sam and himself.

\---------------------------------------------------------------------------------------

Their first year of college goes better than they expected. Charlie is majoring in Molecular Biology and Dean is majoring in Finance. Both their grades are excellent and they come home to visit during all the school breaks and holidays. Charlie’s aunt doesn’t keep in touch and Charlie might as well be Dean and Sam’s actual sister and Bobby’s daughter.

Their second year semester begins and Dean changes his major to Nursing. His roommate Jimmy moves out and another guy named Gabriel moves in a week later. Dean thinks he’s a little annoying but a couple months later he decides as far as he can tell he’s not a bad guy. Dean starts seeing a girl he met in his English class named Lisa. She has dark hair and sometimes it’s hard for him to look at her because she reminds him of Cas. She’s the first girl he’s gone out with since they broke up.

One day after his classes he gets back to their dorm and Gabriel apparently has a friend over to hang out. Dean sighs but just sits down on his bed and tries to ignore them to start on his homework.

“Gabe, you really suck at this game, you know? The other guy says.

“No way, you’re just cheating!” Gabe accuses laughing.

“Wow, sore loser much?” Gabe’s friend asks, chuckling.

Something about that laugh draws Dean’s attention away from his textbook. He takes a second then brushes it off.

“Fuck you, Cas!” Gabe says a few minutes later.

‘Cas?’ Dean thinks as he hears the name. His eyes dart back over to the two guys and his heart is beating rapidly. ‘That’s a weird coincidence. How many names can be shortened to Cas?’ he thinks, trying to get back into his work.

About 20 minutes later, he hears that laugh again. Then Gabe gets up and goes to the bathroom.

“Hey man, I’m Dean.” Dean says, trying to kill the awkward silence in the room.

“Cas.” the other guy says. His voice sounds a little odd, now that he’s paying attention. Kinda sounds like when a kid tries to force their voice to sound deeper. 

Dean shrugs it off. “So what’s Cas short for?” he asks.

“Castiel.” The other boy replies, seeming reluctant to answer.

‘This guy’s weird.’ Dean thinks. ‘Whatever.’ he goes back to his work.

This Cas guy starts being around a lot and Dean thinks he actually seems pretty cool. But when he interacts with Dean, especially if they’re alone he always acts super weird and awkward. Dean thinks he looks homeless because he’s always wearing really loose baggy clothes. He was raised not to judge people though, so he overlooks it.

Several months later, he recognizes the ‘new’ Cas in one of his classes. Dean knows he hasn’t seen him in that class before now. “Cas Novak” their professor calls out when passing out their most recently graded test papers. Dean’s head jerks up and he sees Gabe’s friend walk to Ms. Sunder’s desk. ‘Novak?!’ he thinks. ‘Could he be related to MY Cas?’ his mind reels. He waits outside the door after class until he spots the same black backwards ball cap and baggy clothes. “Hey, Cas.” Dean says following him.

The guy turns around and Dean’s eyes go wide. Mouth dropping open as he sees none other than his ex from high school standing in front of him. He’d never gotten a chance to really see the face of Gabe’s friend before thanks to shitty lighting in their doom plus him only coming over at night. “CAS?!” he asks, suddenly feeling like he can’t breathe.

Cas turns and rushes away without a word and Dean can’t help but follow. “Cas, wait! Please.” he insists. Cas goes out the door and into the parking lot and Dean still continues to follow. When he walks out the building door, he almost runs straight into Cas who’s now standing in front of him.

“What do you want, Dean?” Cas asks, looking and sounding annoyed.

“Cas, what….” he looks again at the clothes and back to Cas’ face and sees the short haircut and he just can’t get any words to come out. He’s beyond confused.

Cas sighs. “You really like wasting my time, don’t you?”

“Damn, seriously?” he asks, suddenly pissed at Cas’ attitude.

“What is it you wanted, Dean?”

“What the hell, Cas? Me and Charlie were so worried about you! We’ve STILL been so worried about you! What the hell happened?! Suddenly you were unenrolled from school and your parents said they didn’t want to associate with you anymore. We didn’t know what to think.”

“I don’t owe you an explanation, Dean. You OR Charlie, and by the way, I’m SO glad to hear that things are going so great for the two of you. I’m thrilled for you both.” Turning to walk away. Dean grabs Cas’ arm gently. “Please.” he insists. “Please talk to me.”

Cas turns and looks at him with another sigh. “Fine. Can we go somewhere? Alone?” Cas asks reluctantly.

“Uh yeah, sure. I’ve still got the impala. She’s parked in the second row over there.” he says pointing.

They both walk over and get in shutting the doors. They sit for several minutes that drag by as Dean looks at Cas waiting to hear whatever the explanation is.

“Remember when I told you I needed time and space?”

“Of course I do.”

“Well, I...I started to question things about myself. That’s when I started to act distant. I was honestly trying to figure things out. That’s why I needed space and time. It wasn’t you, not at all. I realized something and well...my parents kicked me out. Told me they want nothing more to do with me and they sent me to go live with some distant cousins.”

Dean silently listens and just waits for Cas to continue.

“I realized I’m transgender, Dean. A transgender guy. My pronouns are he/him so please don’t refer to me by ‘female’ or she/her pronouns.”

“Wow, I...I uh don’t really know what that means, honestly.”

Cas keeps talking and tells Dean about Gender identity vs sex at birth and the basics of what it means to be transgender.  
“Thanks for talking to me and telling me about all this, Cas. I’m sure it was hard to try to figure that stuff out about yourself. I’m sorry your parents reacted so shitty.”

“So you’re not like freaked out or disgusted by me now?” Cas asks.

“No, why would I be?” Dean answers honestly.

Cas grins but quickly tries to hide it. “I gotta go.” he says, climbing out the passenger side.

“Do you think maybe we can talk again sometime?” Dean asks, unable to hide the hopefulness in his voice. 

Cas looks back at Dean and sighs before looking away. “I don’t think so though, Dean.” he answers, walking towards his next class.

Dean sighs and feels the familiar aching in his chest. Somehow it feels like he’s just lost Cas for the second time.


	7. Chapter 7

The following day Dean goes to Charlie’s dorm because he just has to tell her about Cas. Knocking on the door to her room, he waits impatiently tapping his foot. He doesn’t get an answer and groans. A few minutes later he's reluctantly heading back down the stairs to leave when he meets her in the stairwell. 

“Hey!” She says, smiling and goes in for a hug.

He hugs back for a few seconds before letting go. “Hey. I was uh, just at your room and obviously you weren’t there.” he chuckles lightly.

“Yeah, I was at the library for a little while. You wanna?” she motions upstairs.

“Sure.” he answers, turning to follow her back to her room.

After unlocking the door she flicks the light on and walks inside with Dean behind her.

She sits on her bed as Dean sinks down on the purple bean bag across from her. 

"So what's up? How are classes going so far?" She asks, curiously.

"Oh, they're going okay I guess. Still too early to tell much yet."

"Yeah, I know what you mean." She answers nodding.

His face suddenly changes and Charlie seems to notice immediately.

"Dean?" She asks, looking worried.

"Charlie, I…" he looks away for a second before forcing his gaze back to her. "I saw Cas." He blurts out finally.

Charlie looks dumbfounded, not speaking. She only blinks as her lips part slightly like she's searching for words.

He takes a deep breath and gives her a knowing look.

They sit silently for several minutes and Dean can tell by her expression that she is trying to comprehend the reality of his words.

"You mean...CAS, Cas?" She finally asks incredulously, her eyes wide with disbelief.

Dean nods. "Yeah." He answers simply.

"Wait, what...how...WHAT?!" She stammers still shocked at the revelation. "Cas Novak- OUR Cas?!"

"Yeah, I know. I was just as shocked as you are. I wasn't expecting to see…" he stops himself. "Him." He finishes trying to be respectful of the 'new' Cas since they had talked.

Charlie cocks her head looking even more puzzled than she was a few seconds ago.

Dean sighs and tells her about Cas coming out to him. He also repeats to Charlie everything he could remember of what Cas had told him about what it means when someone is transgender.

She sits, not speaking for a minute or two then finally she looks back to him. "So, that was what she-he was dealing with when he was pushing us both away? And that was why-"

Dean finishes her thought. "Yeah her-his parents kicked him out and shipped him off to go live with some cousins."

Charlie's hands cover her mouth as her eyes go wide again at what she’s hearing. "Oh my God! Poor Cas!" She must have...er HE must have felt so alone and hurt!" She exclaims with pity in her tone.

"Yeah, I'm sure she..dammit..he did. I know I would have." He admits, trying to think of himself in that situation. "I can't imagine how hard it must have been. And on top of that Cas thought we both betrayed him. And apparently he still does."

"Wait, what? Why didn't you tell him it wasn't true?!" Charlie asks, standing up and almost yelling.

"I told him how worried we were and that we still have been about just what the hell happened. If he was okay and everything. Apparently bringing you up just confirmed it for him and he assumes we've been together since then." Dean says, pinching the bridge of his nose.

"We HAVE to find him and explain it was a misunderstanding."

"I don't think that's gonna work, Charlie." He says with a disappointed sigh.

"Why not?" She asks, giving him a disapproving look.

"I asked Cas if we could talk again sometime and...well he basically said no."

I don't think he wants anything to do with us. He still seems just as pissed and hurt as when it happened. I don't think he'll be willing to listen and even if he is...I don't know why he'd be more willing to believe us now than he was back then."

We have to try Dean!" Charlie insists.

He shrugs. “Maybe you’ll have more luck than I did.” Dean tells her.

“So that’s it? You tried ONE time and now you’re giving up? I know you still miss him, Dean. Wait, don’t tell me...you’re suddenly confused about your feelings because he’s trans?” She asks defensively.

Dean doesn’t know how to answer. ‘IS that why?’ he thinks. He opens his mouth to deny it but he can’t manage to find any words.

“Are you SERIOUS right now?!” She asks, obviously pissed.

“I mean...I don’t….Charlie, I…” He struggles. He’d never been able to admit to her that he sometimes felt attracted to guys. He’d never acted on it but that didn’t mean he’d never wanted to. Or that he never considered it.

“You know what Dean, I have something I need to tell you and I need you to be honest with me. BRUTALLY honest, okay? This is something I’ve never told anyone before and if you have a problem with it I deserve to know the truth.” she says sounding incredibly upset, possibly on the verge of tears.

Dean wonders what she could possibly be about to tell him that she thinks he might have a problem with. “Okay.” he agrees.

“I like girls.” Charlie blurts out suddenly.

Admittedly he’s a little surprised. “Okay, I can’t say I was expecting that, but….why would you think I would have a problem with it? Who you date or whatever, has nothing to do with me.” he answers.

Relief floods Charlie’s expression. “Really? You don’t like...think of me differently or something?” she asks hopefully.

“Of course not.” He answers.

“Dean, there’s a reason I decided to tell you that now.” she admits.

He cocks his head and his mouth suddenly feels like the Sahara. “What do you mean?” he asks as his heart begins to race. A panicky feeling spreads throughout his entire body.

“Sometimes back in school, after we got close...I could swear I caught you a few times looking at guys like...kinda like you might be into them.” she admits sheepishly.

Dean’s not sure why he’s so scared to admit the truth to her. Especially considering the fact that she literally just came out to him about liking girls. “I’m not gay, Charlie.” he answers defensively, not able to make eye contact.

“I know you’re not gay, but...it’s possible to like girls AND guys, you know.” she tells him.

He takes a deep breath. “So, are YOU one of those people, Charlie?” he asks.

“No. I don’t see guys like that, Dean. Do you?”

His eyes dart to the floor before he forces himself to look back at her. “yeah...I ...I guess I do. I kinda always have. And...I’ve never told anyone that either.” he admits.

“So, you still have feelings for Cas, right?”

“You know I do.”

“Then what’s stopping you from telling him?”

“I have a girlfriend.” he says weakly.

“Nobody says you have to marry him.” Charlie answers. “But he does deserve the truth. About what really happened back then, AND about how you still feel about him.” She adds.

“You’re right, he does.” Dean agrees.

“Okay, so now we just need to make a plan.” Charlie says.


	8. Chapter 8

Cas tries to focus on his classes, but knowing that Dean is here at the same university is making it really hard to concentrate. The class Dean has with him, it seems he is keeping a distance and Cas is grateful for that. Still, he can’t deny that there are lingering feelings. Even after years apart, it still hurts. He still loves him. ‘Maybe the pain will always be there.’ Cas had thought. After his last class, he’s walking back to his dorm when he hears someone calling his name.

“Cas?” Charlie says.

Turning around, Cas spots his former best friend. The girl who he’d trusted more than anyone and she’d betrayed him. The very same ‘friend’ who had spent the night with Cas’ boyfriend. He couldn’t help the anger, resentment and pain bubbling to the surface at seeing her here. Cas sighs. “Dean didn’t mention that you were studying here too. Guess I should have known.” he says turning away.

“Cas, can we talk?”

“I don’t have anything to say to you, Charlie.” Cas answers snarkily, turning again.

“Please. I’m begging you.”

Cas scoffs and turns back to look at her. “And why would I want to listen to anything YOU have to say? Can you give me ONE good reason why I should give a single FUCk about whatever it is you want from me?”

“Cas, Dean told me about what you talked about. About your parents and..all of it.”

Cas sighed and shook his head angrily. “Of COURSE he did. Jesus, what is it with you two? Just can’t let me move on with my life. Just let it go?”

“Give me 5 minutes, and if you don’t like what I have to say, or you choose to still not believe me about what happened that night, I’ll never bother you again. Dean too.” Charlie offers.

Cas looks unimpressed, but he reluctantly considers. He figures this way at least he’ll have some peace once they finally just let him live his life. “3 minutes.” Cas offers.

“Okay, do you wanna talk right here, or…” Charlie asks, looking around.

Cas sighs. “Follow me.” He leads the way to the building his dorm is in. Charlie follows him inside and she sits on the couch as he remains standing. “Well?” he asks, impatiently, arms crossed.

“Okay first I wanna say I’m sorry. I never should have left that night. I should have been more patient. Tried to be more understanding. But..I was hurting. You were shutting me out and...I was scared of losing you, Cas. You were my best friend.”

Cas’ face doesn’t change, still just looking at her and wishing for this to be over.

Charlie sighs. “So, what REALLY happened that night...I got mad. I saw Dean leave upset and I KNEW exactly why. I didn’t know what was said, but I’d been watching as you were around him less and less. I saw you pushing him away the same way you were with me. So I got mad. For me and for him too. I felt bad for him because I knew he didn’t know what was going on with you anymore than I did. I thought he needed a friend. Especially since I understood what he was going through.”

“Time’s almost up.” Cas lies. He wasn’t actually counting the time, but the very little patience he did have was already wearing thin.

“I followed him out and I DID leave with him. He drove us to an old run down house. We talked about you. We were both frustrated and hurt. We DID end up going back to his house, but it was totally innocent. We started drinking and both passed out. When we got up the next day, we were sick, hungover and throwing up. Dean’s dad wasn’t too thrilled that we had been drinking especially enough to get trashed. Bobby took me home that morning and that was it. I decided that I was going to give you more time and try to keep being patient and...then you had heard the rumors and wouldn’t let me explain. Dean called me later and told me you’d told him the same thing. You wouldn’t listen to either of us and we were both devastated to have lost you. We started hanging out and actually became friends. Best friends even. Then next thing we know, you’re gone and nobody knows where or why. And Cas, I’m SO SORRY you had to go through all of that.”

Cas wasn’t sure why he wanted to believe her story, but it couldn’t be true. He desperately wished it was true, but he couldn’t allow himself to hope. Her last words caused rage to spread through his veins. He heard the pity in her tone and he didn’t want any pity from HER. ESPECIALLY not from her. “I don’t need your PITY.” he spat the words at her.

“I would have never thought your parents-” Charlie started but Cas cut her off.

“Yeah, I’m sure you can’t imagine how you could ever live without your parents that actually give a shit about you. Actually love and spend time with you. How bad it hurts to lose your family!”

Charlie’s face changes, full of pain. Instantly, tears stream down her face and she sobs heavily. She hides her face behind her hands.

Cas actually feels bad now for making her cry. He kicks himself for feeling sorry for her. The anger is still there and he feels the need to taunt her about her probably fake tears. He’d never once seen Charlie cry like that before, so he tells himself she’s just faking. “Oh, come on. Stop being dramatic. Fake tears aren’t going to convince me that you’re telling the truth.” he says, instantly regretting how hateful the words are.

“My parents died, Cas. There was a car wreck a few months before graduation.” Charlie manages to cry out.

Cas’ heart sinks and he immediately feels like the biggest douchebag on the planet. “Oh my god, Charlie I...I didn’t know.” he says, his tone much different now. He sits beside her and before he realizes what he’s doing, he puts his arm around her. “Shit, I..I’m an asshole. I’m sorry.”

A few minutes pass and Charlie seems to get herself under control. “I know you didn’t know. Or well, I assumed you didn’t.”

“I’m so sorry, Charlie.” he adds.

She only nods. Looking back up at him, she sniffles and gives him a sincere look. “And by the way, I’ve never been into Dean like that. I never told you but...I’m actually a lesbian, Cas. I like girls.”

Cas moves his arm back down to his side. “Oh. I..yeah, I never knew that.” he answers simply.

“I, uh...I only just came out to Dean yesterday. You’re only the second one to know.” Charlie adds.

Cas doesn’t know what to say.

“I’ve really missed you.” Charlie adds.

Cas sighs. “I’ve missed you too.” he admits, looking down to the floor. “So…” he chances looking back at her. “Really, that’s all that happened that night?”

“Yeah. It really is. And even if I WAS into guys, I would NEVER have done that to you, Cas. And I know Dean wouldn’t have either. His eyes always lit up whenever you were around each other. Yours did too.”

“So... you believe me?” Charlie asks.

“Yeah, I do.” Cas admits. “I’ve been carrying around all this pain, anger and hurt all this time. Believing you’d both betrayed me.

Charlie takes his hand. “I’m so sorry you had to go through all of that alone.”

“And I wish I’d been there for you when….” Cas doesn’t finish.

Charlie looks down. “Me too. But it wasn’t your fault you left. And thankfully, I wasn’t alone through it. Dean was there for me. Him, his dad and Sam...they took me in. They’re practically family now.”

“That’s so great.” Cas says sincerely. It feels so strange now to have his chest feel so light knowing the truth now. They hadn’t betrayed him. “So, you don’t have an issue with...the ‘new’ me?” Cas finally asks.

“Of course not.” Charlie answers.

They end up talking for hours, catching up. Cas feels like he’s finally got his best friend back. It feels so good to have Charlie be back in his life.

Suddenly he has a realization. “Oh, fuck!”

“What is it?” Charlie asks, concerned.

“Dean. I was such an ass to him. God, why didn’t I just listen to you both way back then?” Cas asks aloud, full of regret.

“You were going through something HUGE, Cas. And...we were teenagers. And I have to admit it DID look bad. We should have just told you about it before you had to hear rumors about what people assumed happened. So, you’re not the only one with regrets. But we’re here now.” Charlie says reassuringly.

“I should talk to Dean.” Cas says with a sigh.

“Yeah, you really should.” she agrees.

“Hell, he probably won’t want to after how I acted.”

“That’s not true, Cas. Trust me. Find him.”


	9. Chapter 9

Cas tosses and turns that night as the wonderful memories of his year with Dean plays through his head. He’s not sure what to expect but he knows Dean deserves an apology. His 3rd class of the day is the one he shares with Dean. Once it starts, Cas can barely pay attention as he waits for it to be over. Thankfully he’d managed to get a seat close to the door, so he’s almost positive he can catch Dean as he leaves. ‘Why am I so nervous?’ he asks himself as he realizes his hands are shaking. He feels so stupid for all the bad things he’d made himself believe about Dean all this time.

Finally their professor dismisses them and he almost runs to the door. He waits just outside, up against the side of the door frame just out of the way. His heart leaps when he sees Dean’s face. Cas opens his mouth to speak, but Dean turns and walks away after seeing him. ‘I deserve that.’ Cas tells himself. He jogs after him. “Dean, wait.” he says. Dean doesn’t slow down before he leaves the building. Cas sighs but stubbornly follows behind. He turns the corner and Dean is standing facing him with his arms crossed and his lips pressed tightly together. His face offers no hints of his emotions. Cas licks his lips and gulps. His heart races as he’s face to face with his high school sweetheart once again.

“What do you want?” Dean asks, his tone harsh.

“Can we talk?” Cas asks, his voice small.

Dean flexes his jaw, dropping his arms to his sides and leaning his hip against the wall. “You made it pretty clear you don’t want anything to do with me.” 

“Look, I...I’m sorry for how I behaved last time. Just...please?” Cas gives a pleading look that Dean never used to be able to refuse. He hopes it still has the same effect on him now.

Dean sighs and bites his lip. “Fine. After you.” he says, holding his arm out toward the parking lot.

Cas leads the way this time, Baby’s still parked in the same spot and they both climb in.

Dean looks at Cas expectantly.

Cas tries to take deep calming breaths. “I talked to Charlie.”

“What does that have to do with me, Cas?” Dean asks with a snarky tone.

Cas knows he deserves Dean’s current tone. “She told me what really happened that night.”

Dean still looks at Cas, his face is unchanged.

Cas sighs and closes his eyes for a moment. He forces himself to make eye contact once again. “Dean I...I’m sorry. I’m sorry I wouldn’t listen. I’m sorry I wouldn’t let you explain back then, and I’m sorry for not listening the other day.

“Don’t worry about it.” Dean answers nonchalantly. “So, is that all? Are we done here?” he asks.

Cas’ heart sinks. ‘Fuck’. “I just...I just wanted to apologize. I should have trusted you.” he answers, once again feeling the familiar ache in his chest.

“Alright, well thanks for that.” Dean says coldly, stepping back out.

“Dean.” Cas tries, stepping out and taking a step toward him.

“Gotta go, meeting my girlfriend at the library.” Dean says not slowing or stopping.

Cas freezes in place and his heart sinks. ‘Of course he has a girlfriend’.  
\-------------------------------------------------------------------------------------

Later that day, there’s a knock on Cas’ door. He figures it probably just Gabe. Opening the door he’s pleasantly surprised to see Charlie. “Hi.” he greets her, stepping to the side to let her in.

She grins. “Hey. So did you talk to him?” She asks, taking a seat beside Cas on the couch.

Cas sighs and closes his eyes for a few seconds.

Charlie’s smile falls, waiting to hear what happened.

“I waited for him after class and apologized.” Cas answers simply.

“And what did he say?” Charlie asks, seemingly hesitant.

“It seemed like it meant nothing to him. Like he couldn’t care less. Said he had to go meet his girlfriend.” Cas says, not really knowing why he included the last part.

“Wow.” Charlie says, looking at Cas sympathetically.

“Yeah.” Cas adds.

“What were you hoping would happen?” She asks.

“I...I don’t know.” he answers honestly. “That it would make me feel better to apologize. That maybe he would react…. differently, I guess. I’m not really sure what I expected.” he sighs. So he has a girlfriend?” he hears himself ask.

Charlie looks like she doesn’t want to answer. “Yeah some girl named Lisa. I’m pretty sure it’s not serious though. I’ve never met her.”

“Guess I shouldn’t be surprised. From Dean’s perspective I ended things over a rumor and never let him explain the truth. He didn’t know what I was going through. How could he be there for me, when I refused to tell him? Then I was just mysteriously gone. Not like I could blame him for being pissed and hurt. Besides, I’m sure he had lots of girlfriends after I left anyway.”

Charlie puts her hand over Cas’. “I think you should try again. Maybe give him a little time first.” she tells him.

“I guess that’s fair.” Cas answers.

\------------------------------------------------------------------------------

Two months later, Cas decides he can’t stand to wait anymore. He picks a day when he knows Gabe won’t be there and a time when Dean will already be in for the night. His heart is thudding loudly in his ears as he climbs the stairs. He forces himself to take a few deep breaths as he reaches his door. Finally he knocks. 

The door opens and the surprise on Dean’s face is obvious. They stare at each other for several seconds without speaking before Dean sighs and moves to the side.

Cas can’t help but feel hopeful at Dean’s gesture. He walks in and Dean sits on the edge of his bed. Not knowing quite what to do, he remains standing. “Look, I...maybe it doesn’t matter to you anymore but- I just needed to let you know I feel terrible. You never gave me a reason to doubt you and...the first time something came up I didn’t even hesitate to believe other people without even listening to what you had to say about it.” He finds himself moving until he’s standing in front of Dean. “I was wrong.” He can’t stop himself from taking a seat next to Dean. “And I’m sorry. I’m SO sorry I hurt you, Dean. I know I was going through my own stuff, but..that doesn’t excuse it.” he reaches out and takes Dean’s hand. He doesn’t even realize what he’s doing until he feels the warmth and familiarity of Dean’s skin against his.

After a few seconds, Dean pulls his hand away. He looks at Cas for several seconds before looking down at the floor.

Cas feels like he can barely breathe. There’s a pull drawing Cas to Dean that’s always been there. Looking at him again now, sitting so close and after feeling his hand against his again...he realizes why he’s still been hurting all this time. ‘I still love him.’ The revelation is bittersweet and he doesn’t know what to do. What to say.

Dean looks back up, meeting his gaze and Cas is shocked to see his eyes full of unshed tears.

Cas’ heart chest aches at the sight of Dean hurting. Knowing he had hurt him had been bad enough, but to see it was far worse.

“I loved you, Cas. I would have never hurt you.” he says finally.

The guilt weighs even heavier in the pit of Cas’ stomach along with something else. ‘Loved. Past tense.’ “I’m so sorry. I wish I could take it back.” Cas tells Dean.

Dean looks away again and sighs. “Yeah well, can’t change the past, right?” he says laughing humorlessly.

“It was a mistake to come here.” Cas says suddenly, stepping away from the bed. He doesn’t look at Dean. He fails to hold back a sniffle as he walks toward the door. “I won’t bother you anymore.” he adds, trying his best to keep his voice even. He opens the door and suddenly it shuts back, pulling out of his hand. He turns and sees Dean standing in front of him, hand on the door beside Cas’ head.

“Don’t go.” Dean says, his eyes pleading. His face is much softer now, full of emotion.

Cas’ eyes close and he licks his lips. “Why not?” he asks.

“I don’t want you to go.” Dean insists, dropping his hand from the door, taking Cas’ hand in his.

“What about your girlfriend?” Cas asks, looking up at Dean through his long dark lashes just like he used to. He pulls his hand away.

“I lied. I wasn’t meeting anyone when I left the other day.”

“Charlie told me her name’s Lisa.” Cas says looking down to the floor.

Dean gently tips Cas’ chin up to look at him. “As soon as I found out you were here I ended things with her.”

“You shouldn’t have done that.” Cas says, looking away again. “It’s not right.” he adds.

Dean sighs. “Please look at me?” he pleads.

Reluctantly, Cas gives in and meets his eyes again.

"She's the first person I've dated since you. It's was only for a few months, and we weren't serious. Cas, I never...you were my first. My only." he admits. And nothing’s changed, Cas. Yeah a lot of things are different now but I mean...I never stopped loving you.” he takes a step back and he gulps, looking to the floor. “I understand if you don’t feel the same, I just...I couldn’t let you leave without letting you know.” There’s a defeated look on his face.

“Do you really mean that?”

“Of course I do.”

“Dean, I…. I can’t be your girlfriend again.”

“I know. But what about being my boyfriend?”

“Are you...are you serious? But..you’re not gay. You don’t like guys like that. I can’t ask you to-”

Dean leaps forward and shuts Cas up with a kiss. The same sparks and tingles that were always between them are still there as their lips are pressed together. Cas pulls away several seconds later and searches Dean’s eyes.

“Actually, I never told you but... I DO like guys. Girls AND guys.” Dean says matter-of-factly.

Cas is on the verge of tears again only this time it’s tears of joy. Hope that he hasn’t felt in years.

“So, how about it? Will you be my boyfriend?” Dean asks.

It’s the first time Cas has seen that incredible smile since high school. He can’t hold back the tears from flowing now as he nods.

Dean wraps his arms around Cas and they just stand there together.

Cas can’t believe this is real. He’s got his boyfriend and best friend back. It feels wonderful to be back in Dean’s arms. “I missed you so much, Dean.” Cas says, finally feeling all the weight off his chest.

Dean cups Cas’ face with both hands and smiles at him. “I missed you too.”

“And Dean.”

“Yeah?”

“Thank you.”

“For what?”

“For being there for Charlie. Thanks for taking care of my best friend while I was gone.”

“She’s my best friend too now, ya know.” Dean says.

Cas chuckles. “So, I heard.”

Dean wraps his boyfriend up in his arms, pressing a soft lingering kiss to his lips. “I love you, Cas.” he tells him when he pulls back to look in his eyes again.

“I love you too, Dean.” Cas says, running his fingers through Dean’s hair. He never thought he’d feel this happy again.


	10. Chapter 10

Cas looks up at Dean, arms around his neck. They’re still standing against the door. 

“You think we can start over?” Dean asks shyly. “Or well..get to know each other again? We can probably skip some steps for ‘new’ relationships.”

Cas chuckles. “I’d like that.”

Dean’s eyes are full of love as he stares into Cas’ still impossibly blue eyes.

“So, do you have classes tomorrow?” Cas asks, laying his head against Dean’s chest.

Curling his arms around his boyfriend, Dean presses his chin against Cas’ forehead. “Might take the day off. Not the end of the world to have a couple absences.” he answers, kissing the top of Cas’ head. “Did you have something in mind?”

“I thought it might be nice to spend the night with my boyfriend.” Cas offers, biting his lip.

“Yeah, I uh…” Dean blushes a little. “Wait, what about Gabe? You sure things won’t be like...awkward or anything?”

Cas pulls Dean’s face down to his, by his collar. He kisses him, deeply- intensely. “We’re just friends.” he assures Dean once the kiss breaks.

Grinning, Dean cups Cas’ face. “I’d love for you to stay over...if you’re sure.”

Nodding, Cas pulls Dean in for another passionate kiss.

Their bodies press impossibly closer together til they both pull away panting. Cas peppers Dean’s jaw and neck with soft kisses. Dean closes his eyes and moans lightly.

“We don’t have to um..I mean, I don’t expect-” Dean starts.

Cas shuts him up by trapping his mouth in yet another kiss. 

Dean instinctually picks Cas up until the smaller boy’s thighs are resting on his hips. Cas moans into Dean’s mouth.

Both lost in the moment, they startle when someone presses against the door almost knocking them over.

“Uh...hello?” Gabe says from the other side of the door.

Cas and Dean chuckle a little before Dean sets Cas’ feet back on the floor. They move out of the way and sit on Dean’s bed.

Gabe opens the door slowly, peeking inside before stepping in. “Oh..hey guys.” he says when he notices Cas and Dean both inside. He eyes them, seemingly taking in the unusual sight. He grins. “So what’s up?”

“Well, uh..I know you two already know each other, but I’d like you to meet my boyfriend.” Dean says, moving his hand over Cas’.

Gabe cocks his head and grins. “I KNEW something was going on with you two! The awkwardness between you both every time Cas was over- it was more than obvious something was up. Hell, I’m happy for you.” he says, sincerity obvious in his tone.

“Thanks, man.” Dean answers.

“I appreciate that, Gabe.” Cas adds.

Suddenly Gabe’s face drops. “Oh SHIT! Does this mean…” he looks worriedly to Dean. “Are you moving out?”

“Uh, I think it’s a little soon for that.” Dean offers.

“Yeah we’re not quite to that point yet.” Cas adds.

Gabe gives a relieved sigh. “I’m so glad! So, Cas you ready for a rematch?” he motions to his tv and gaming system.

“Maybe later. I think Dean and I are going out for a little while.” Cas answers, giving Dean a mischievous look. Getting up, he reaches for Dean’s hand.

Dean takes Cas’ hand, jumps up and follows Cas to the door. “See ya later.” he offers as he’s practically dragged into the hallway.

“So where’re we headed?” Dean asks as he’s pulled out of the building.

Cas turns and smiles at Dean without answering.

Dean chuckles, allowing his boyfriend to continue to lead him.

Once they step into the parking lot, Dean grins. He realizes that they are indeed walking straight towards the spot Baby is parked in.

When they’re close, Cas turns to face Dean, pulling him against him. His back is pressed against the passenger door of the impala.

“If I didn’t know any better I’d think you brought me out here to get me alone.” Dean teases. 

“Maybe.” Cas teases right back. He looks up at Dean through his long lashes, like he knows always drives him crazy. “Get in.” he orders.

Dean obeys, getting in and sliding over to the driver’s seat. Cas gets in on the passenger side, then climbs into Dean’s lap. He straddles Dean and slides his hands up under his shirt, caressing the bare skin of his chest. He ghosts his lips down Dean’s neck, then nibbles his earlobe before rocking his hips against the larger boy.

He gasps, grabbing Cas’ thighs and kissing him wet and dirty as he helps Cas rock against him. Then kissing and nibbling Cas’ neck he lets out a low moan. “Fuck, Cas.” he says, breathlessly.

“Say my name, Dean. Please, baby.” Cas begs, continuing to practically ride Dean’s still clothed erection.

“Castiel.” Dean says, his voice low and husky.

“Mmmmm.” Cas hums happily. “God, baby.” he says, sucking in a quick breath.

“C’mere.” Dean says, turning Cas to face away from him on his lap. He leans Cas against him til his back is fully against Dean’s chest. 

“Wha-” Cas starts to ask.

He pulls Cas’ shirt up a little, baring his stomach. Dean slips his hand a few inches down beneath the front of his jeans and boxers against his skin. Not knowing if this is something Cas still likes, Dean pauses.

“You want me to touch you Angel?” Dean asks.

Tingles spread as Cas remembers how good Dean’s fingers always felt. “Yeah, finger me.”

Given permission, Dean pushes his hand down farther til his fingers brush against coarse pubic hair. He can already feel the wetness and heat from his boyfriend’s arousal. Cas is unable to hold back a moan when Dean easily slips two fingers inside.

Cas gasps, dropping his head back to rest against Dean’s shoulder. Eyes closing immediately as he feels the digits pushing deep inside him.

“Mmmm so wet for me, Cas.” Dean praises as he adds a third finger.

Cas is completely lax against his boyfriend’s body. Pleasure clouds his mind, constant moaning that he doesn’t even try to control. He already feels like he’s going to cum soon and it’s been SO long since the last time anyone but his own hand or toy has got him off.

“Feel good? Huh? You like when I finger you, baby?”

“Y-y-yes.” Cas barely manages to answer through panting breaths.

“You gonna cum, Angel? Or do you want my tongue? Tell me what you want, sweetheart.” Dean says, licking and sucking on Cas’ neck as his own dick is fully hard and begging to be touched.

“Want you, Dean. Need to feel you inside me.” Cas whimpers. "And I haven't, uh...you're my only too, Dean." he adds hesitantly.

Dean roughly fingers Cas deeper, causing the smaller boy to moan louder as he gets closer to his orgasm. “Oh, god Cas. Want you so bad. You wanna ride my cock? Be a good little slut for me, baby?”

“Fuck yeah.” Cas answers, shuddering at the familiar dirty talk from his boyfriend. He pulls back and turns enough to get Dean’s jeans unzipped and unbuttoned, pulling his heavy, dripping cock out. Quickly he undoes his own jeans, pushing them along with his boxers down and off and climbing back onto the larger boy’s lap, facing him again.

He slowly lowers himself, feeling the head of Dean’s dick press against his drenched opening. He gasps and Dean moans as Cas lets himself sink down, taking Dean’s full length inside him.

Immediately Cas rocks his hips again, lifting up slightly, then pressing back down hard. Repeating the motion again and again, Dean holds Cas’ thighs firmly, helping his movements and rolls his head back.

Breathing hard, they keep thrusting together. Cas is holding Dean’s shoulders to steady himself as he leans in and kisses Dean.

Dean plants his feet on the floorboard and begins meeting Cas’ thrusts, fucking up into him.

Cas’ mouth drops open and his eyes close as he moans even louder, clinging tighter to Dean’s shoulders. “Oh fuck, baby. Fuck, fuck fuck, Dean! Oh god. Fuck! Baby!” Cas begins chanting through bated breaths.

“You feel so good, Cas.” Dean praises.

“Feels so good when you’re inside me.” Cas answers immediately.

“Tell me, baby. Tell me you’re a slut for my cock.”

“Oh yeah, I’m a slut for your cock, baby. Only for you, and your fucking perfect cock, Dean.”

“God, you’re still so tight for me baby. So perfect. Missed you so fucking much, Cas.”

“Ahh..Missed you too, baby. Missed you so much.”

“I’m getting close, Angel. You want my cum in you? Still my fucking cumslut, baby?”

“God, yes Dean. Fucking cum in me. Fill me up, baby.”

Dean grips Cas’ hips tight enough to bruise and begins slamming the smaller boy’s body down into him as he continues thrusting up into him.

Cas moans as his body is jarred repeatedly by Dean’s cock crashing against his inner wall, feeling right on the edge.

Dean unintentionally begins growling as he chases his release.

“Fuck, yes baby. Gonna make me cum. Fuck!” Cas wails.

“Yeah cum for me, baby and I’m gonna fill you up just like you like. My good little whore.” Dean says through clenched teeth.

“Fuck yeah.” Cas agrees. Just then he moans so loud it’s almost a scream then stills. Dean, feeling his boyfriend’s inner muscles spasming, is tipped over the edge. He cums harder than he has since the last time he and Cas were together.

Cas tries to catch his breath, falling limp against Dean’s muscular frame.

Dean wraps his arms around the smaller boy and runs his fingers lightly through his hair. “So good for me, Cas. Love you so much.” he praises between deepening breaths.

“Love you too.” Cas answers, eyes closed feeling incredibly drowsy. He rests his head on Dean’s chest once again. “Ugh. Carry me back up to bed?” Cas asks, then laughs.

“Sure, just lemme catch my breath first.” Dean answers.

“I wasn’t serious.” Cas says, seeming a little nervous.

“Why not?” Dean asks curiously.

“Dean.” Cas in a more serious tone.

“Sorry Angel, just thought it might be romantic.” Dean offers, sincerely.

“Thank you for that. But please don’t carry me.” Cas says, softening his tone.

“No problem sweetheart. I don’t wanna make you feel uncomfortable.” Dean answers sweetly, kissing Cas’ forehead. “So, my dirty talk..I didn’t like make you feel bad or weird or anything right?”

Cas smiles and kisses Dean’s lips. “No, I liked it. But thank you for checking with me.”

“Of course, beau- oh, um..I’m sorry baby. Would you like it if I call you handsome?”

“Very much.”

“You got it, handsome.”

“You’re such a dork. My sweet sweet dork”

“That’s right, I’m all yours.” Dean says grinning, then kisses him.

“And I’m so glad that you are.” Cas says as he smiles against Dean's lips.


	11. Chapter 11

Bobby, Dean and Sam shuffle around the house setting boxes down and going back outside to grab another. 

“How many more?” Sam complains.

Dean chuckles, patting his brother on the back. “Oh come on, a big strong guy like you should have no problem.”

Bobby rolls his eyes and shakes his head as he walks outside.

“Why can’t Cas or Charlie help move their own stuff again?” Sam asks a little while later.

“Because they have class and we could only reserve the truck for today, before they’re closed for the holiday weekend. And I’m the only one who’s free until late afternoon.” Dean answers.

“It’s no problem, we don’t mind helpin’.” Bobby says, looking at Sam expectantly.

Sam’s only reply is a scoff as he carries a box down the hallway.

“So, what do you think of Charlie’s new girlfriend? Is she nice?” Bobby asks.

“I haven’t really been around her much yet, but she seems pretty cool.” Dean replies.

“Well, as long as she’s good to Charlie, that’s good enough for me.”

“Yeah as far as I’ve seen and the way Charlie talks about her, Jo seems to be real good to her.” Dean answers with a smile.

“Good. I’d hate to see her go through another like the last one.”

“Definitely don’t think Jo is anything like Dorothy. It was tough on Charlie, but we all gotta get our heart broken sometime, right?”

“I think we’re down to the last few, FINALLY.” Sam whines.

“Geez, Sam, do you really have to complain the WHOLE time?” Dean asks annoyed.

Sam rolls his eyes, walking past with a huff.

“Alright, cool it you two. We’re almost done.” Bobby scoffs.

“I’M fine, Dad. He’s the one being a big baby.” Dean insists, carrying in the next to last box.

“I am NOT being a baby!” Sam protests, the last box in hand.

“Oh, chill, Sammy.” Dean groans.

“For the LAST time, it’s SAM not SAMMY, Dean.” Sam says.

“Okay, okay. Zip it!” Bobby huffs. “Now, put the damn boxes down and you two are gonna go get some lunch. I’m getting a break from you two griping at each other and you guys are going to spend some quality time together. I’m drivin’ the uhaul back and dropping it off. I’ll be at the diner a few blocks away for lunch so come get me after you eat SOMEWHERE ELSE.”

Dean and Sam both begin to protest.

“I don’t wanna hear it. I mean it.” Bobby says before leaving in the now empty uhaul.

The brothers groan in unison.

“So, Sammy- Sam, what is up with you anyway?”

“Nothing’s UP with me.”

“Come on, talk to me. Is it Jess? You guys having problems? School?”

Sam doesn’t answer, just plops down onto the couch.

Dean sighs, sitting down in the kitchen chair across from Sam. “Seriously. I guess we haven’t exactly had much time to just hang out and talk about stuff in a while.”

“It’s fine. You have your own life going on and I’m just a dumb kid.”

“That’s not true.”

“Sure feels that way. We used to be close, but..now it’s like you don’t have time for me and you don’t even care.”

“Hey, I care. Look, I’m sorry if I don’t check in or whatever as much as I should. I’ll do better, okay? Maybe we can..I don’t know, hang out at least once a month. Even if it’s just to watch movies and order a pizza or chinese or something. How’s that sound?”

“Whatever, it’s cool. You don’t have to change your plans on MY account.”

“C’mon man, it’s not like that. Really. I’m sorry if I’ve made you feel left out, okay? I promise to do better.”

Sam looks up at him. “Yeah, okay. We’ll see.”

“Alright, well you wanna go out, or order in? We can start on that whole ‘brotherly bonding’ thing before we go pick Dad up and while the house is empty. What’dya say?”

“That’d be cool, I guess.”

“Cool.”

\---------------------------------------------------------------------------------------------

“Thanks for doing all the heavy lifting, man.” Charlie says patting Dean on the back. “Oh, hey uh if you guys don’t mind Jo’s gonna come help me unpack and set up my room. Maybe even stay the night?”

“I don’t mind.” Cas answers, putting his arm around Dean.

Dean chuckles. “You don’t need our ‘permission’ for your girlfriend to stay the night, Charlie.”

“No, I know. Just wanted to, I don’t know, like not be rude since it’s not just my place. Figured I’d check with you two to make sure you’d be cool with it.”

“We appreciate that, Charlie.” Cas adds.

Charlie grins. “Cool, thanks guys.” she says before heading to her room.

“So how was it? How’re Bobby and Sam?” Cas asks, walking beside Dean as they move to the couch.

“It was fine. Dad’s..Dad, you know. And Sam- eh, he’s feeling a little left out. Told me he feels like I don’t have time for him in my life anymore.”

“Aww poor Sammy. I mean we do stay pretty busy.”

“Don’t let HIM hear you call him that. He’s insisting on just SAM now. And yeah, I promised to make more of an effort to make sure we have some time to just hang out though.”

“I think that’s a great idea. I’m sure you both need it. Must be a big adjustment to go through for him, you leaving for college with how close you guys always were.”

“Yeah, I’ve definitely missed him but I guess I assumed he’s growing up he’s got his own life too and he’d be too busy to think about me.”

“He’s not gonna outgrow you, Dean. Sure you’re gonna piss each other off and get annoyed at each other and even need your own space, but that doesn’t change anything.”

“Thanks, babe.” Dean says, hugging Cas close.

“Of course, baby. So, you wanna tackle everything tonight or wait til in the morning?”

“Ugh. I mean, I don’t wanna do it at all, but I guess if we wanna sleep on a made bed we gotta unpack our shit so we can find the sheets and everything.”

“And THAT’S why you should pack things by room.” Cas insists.

“Yeah, yeah. You know the best way to do everything.” Dean teases.

“No, it just makes sense. You’re the only person I know who literally just shoves everything in a box ‘til it’s full then does that with every box until they’re all packed.” Cas accuses, laughing.

“Sure made packing quicker.”

“But it’s gonna be a BITCH to unpack though.”

“Alright, that’s enough critique. C’mere you!” Dean says, attacking Cas with kisses. He knocks the smaller boy back against the couch, laying on top of him pressing against him. He moves to Cas’ neck and starts kissing and sucking down to his collarbone.

Cas gasps, pulling Dean closer.

“Wanna move this to the bedroom?” Dean asks with a wicked grin.

“Well, it’d be nice to have the bed.” Cas laughs.

“Alright, smartass. But we don’t need a bed.” 

Dean gets up and Cas follows, hand in hand to their room. Cas closes the door and Dean presses him against it, crashing their mouths together. “I missed you today.” he says against Cas’ lips.

“I missed you too, baby.” Cas answers. He pushes Dean back and presses him back against the wall.

“Mmmm. I love it when we fight for dominance.” Dean says, chuckling.

“My turn, this time.” Cas says, pulling Dean’s shirt off over his head.

“Deal.” he agrees, undoing Cas’ pants.

“So glad we have some privacy now.” Dean says as he unbuttons Cas’ shirt.

“Definitely.” Cas agrees, starting on getting Dean out of his jeans.

The doorbell rings. “Jo.” Dean and Cas both say, then laugh going back to kissing.

Finally down to only their boxers, Cas slips his hand beneath Dean’s waistband and teases his fingertips along his boyfriend’s length.

Dean huffs out a sharp breath, eyes half lidded. He pulls Cas’ boxers down his thighs, then easily slips two fingers inside. 

Cas gasps and begins to moan softly as Dean fucks his fingers into him. He tightens his grip slightly and jerks Dean’s cock in earnest, drawing delicious noises from him.

“Fuck, Cas.” Dean says, adding a third finger, then increasing speed and pushes his digits as deep as they’ll go. Cas pulls Dean’s hair with his free hand as he pumps Dean’s cock faster.

“Oh god, baby. I’m gonna cum.” Cas whimpers.

Dean pulls Cas’ hand away from his length before wrapping his free hand behind Cas’ back pulling him closer. “Cum for me, Angel.”

Cas drops his head to Dean’s shoulder and moans against his skin to try to muffle the noise.

“Fuck yeah, baby cum for me.” Dean urges.

Cas feels his muscles spasm and scratches Dean’s shoulder with the need to hold on. Wetness drips down Dean’s fingers and he pulls them out, sucking them dry with a filthy moan.

“Fuck me, Dean.”

Dean smirks and drops to his knees.

“Oh, god yes.” Cas says, letting his boxers drop to his ankles. Dean helps him pull them off then starts kissing up Cas’ thighs. “Fuck.” Cas moans.

Dean kisses and sucks bruises along Cas’ inner thighs as he moves toward his wet heat. He stops and stands back up then picks Cas up and sets him on top of the short dresser in their room. Cas leans back and Dean helps him scoot to the edge. “Sorry, I didn’t mean to..” Dean starts to apologize for picking him up since he said before he didn’t want him to.

“It’s okay.” Cas assures him and kisses him deeply licking into Dean’s mouth.

Dean pulls back and sinks back to his knees, holding onto Cas’ thighs he buries his tongue and moans at the wonderful taste of his boyfriend’s cum. He laps it up and tongue fucks his eager sopping wet hole, drawing stuttered breaths from his boyfriend.

“Oh fuck. Yeah, baby.” Cas moans, gripping Dean’s hair again.

Moaning, Dean continues with even more eagerness. No doubt, he’s driving Cas toward another orgasm. He reaches up and rubs against Cas in just the right place to add to the build up. 

Cas unintentionally grinds against Dean’s face as he’s on the verge of cumming a second time.

Dean pulls back for a split second. “Yeah, cum in my mouth, sweetheart.” he pleads going back to his task.

A few more seconds and Cas cums with hardly a noise. He’s overcome with the sensation of his release as well as feeling his boyfriend’s determined mouth drinking it down.

When Dean finally pulls away, his lips and chin are soaked and he’s panting. “God, you taste so fucking good, Cas.”

Cas pulls the hair he still has hold of to pull Dean’s head back to look at him. His pupils are dilated and desire is written on his face. “Fuck me.” he somehow pleads and demands.

Cock achingly hard and dripping pre-cum Dean pulls Cas down, turns him around and bends him over the dresser. “You ready for me, baby. You like being a slut for my cock?”

“Yeah, baby I’m a whore just for you. Gimme that thick perfect cock- need it.” Cas begs.

Dean easily presses inside and grips Cas’ hips. “Oh, god. So fucking wet. Still so tight, baby. Always feel so fucking good, Cas.”

Thrusting deep and rough they moan together. “Not gonna... last long.” Dean manages, speeding up and gritting his teeth.

“Good. Fill me up, baby. Need your cum.” Cas moans.

“Fuck yeah. Gonna give you all my cum, baby. It’s all for you.” Dean promises.

Moaning and panting is all they can do for the next few minutes as their release builds up. Finally, they both still and Dean leans over Cas, dropping his head to Cas’ back. After a moment, he presses a kiss against his shoulder.

“I fucking love you.” Dean says, pulling out slowly.

Cas chuckles. “I fucking love you too.”

They clean up then head to the kitchen. Charlie and Jo are in the living room sitting on the couch. When they walk into the room, the girls smile silently as they eye them. “Might wanna put some music on or something next time.” Charlie blurts out.

Dean and Cas blush but Dean’s face is hidden behind the fridge door. “Who wants to order pizza?” he says, changing the subject as he closes the fridge.

Cas chuckles, kissing Dean and taking his hand.

“Sure. As long as you guys washed your hands after all that.” Jo says.

Dean hides his face against Cas’ neck causing Charlie and Jo to laugh hysterically.


End file.
